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Method for selectively removing carbohydrate compound anomer carbonyl by FeCl3.6H2O

A technique for anomeric carbonyl compounds, which is applied in the field of selective removal of anomeric carbonyl groups from sugar compounds by ferric trichloride hexahydrate (FeCl3 6H2O), to achieve the effects of low price, less pollution, and simple and easy operation

Inactive Publication Date: 2009-10-14
RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods are either very expensive reagents, or very toxic, and the pollution to the environment is very serious, which violates the sustainable development strategy currently advocated

Method used

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  • Method for selectively removing carbohydrate compound anomer carbonyl by FeCl3.6H2O
  • Method for selectively removing carbohydrate compound anomer carbonyl by FeCl3.6H2O
  • Method for selectively removing carbohydrate compound anomer carbonyl by FeCl3.6H2O

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Experimental program
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Effect test

Embodiment 1

[0015]

[0016] Dissolve carbohydrate compound 1 (1.0 mmol) in CH 3 CN, then FeCl was added to the reaction solution 3 ·6H 2 O (1.0mmol), heated to reflux for about 1 hour. The progress of the reaction was monitored by thin layer chromatography. After the reaction, add ethyl acetate to dilute, and then use saturated NaHCO 3 The aqueous solution was neutralized, the organic phase was collected, dried, concentrated, and separated by column chromatography to obtain Compound 2 (0.9 mmol, 90%). The molecular weight of Compound 2 was 348 according to mass spectrometry.

Embodiment 2

[0018]

[0019] The carbohydrate compound 3 (1.0 mmol) was dissolved in CH 3 CN, then FeCl was added to the reaction solution 3 ·6H 2 O (1.0mmol), heated to reflux for about 0.2 hours. The progress of the reaction was monitored by thin layer chromatography. After the reaction, add ethyl acetate to dilute, and then use saturated NaHCO 3 The aqueous solution was neutralized, the organic phase was collected, dried, concentrated, and separated by column chromatography to obtain compound 4 (0.95 mmol, 95%), and the molecular weight of compound 4 was 290 according to mass spectrometry.

Embodiment 3

[0021]

[0022] The carbohydrate compound 5 (1.0 mmol) was dissolved in CH 3 CN, then FeCl was added to the reaction solution 3 ·6H 2 O (2.0mmol), heated to reflux for about 2 hours. The progress of the reaction was monitored by thin layer chromatography. After the reaction, add ethyl acetate to dilute, and then use saturated NaHCO 3 The aqueous solution was neutralized, the organic phase was collected, dried, concentrated, and separated by column chromatography to obtain compound 6 (0.80 mmol, 80%), and the molecular weight of compound 6 was 636 according to mass spectrometry.

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Abstract

The invention provides a method for selectively removing carbohydrate compound anomer carbonyl by FeCl3.6H2O, which is shown as a formula I. The method can play an important role in carbohydrate medicine synthesis.

Description

technical field [0001] The invention relates to the field of synthesis and application of important intermediates of carbohydrate compounds with biological activity. Background technique [0002] Natural oligosaccharides or sugar conjugates have good biological activities in terms of physiology and pharmacology (Schmidt, R.R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-23), and the more attention they receive getting closer. So far, there have been a lot of literature reports on the synthesis of carbohydrate compounds. In these synthetic strategies, a very important step is the regioselective removal of anomeric carbon-oxygen-acyl groups, and then converting the obtained anomeric carbon-hydroxyl compounds into active reaction donors for the synthesis of oligosaccharides. For this reason, there are many method reports that can realize this purpose, for example, ammonia (Mikano, M.Carbohydr.Res.1989,191,150-153), benzylamine (Conchie, J.; Levvy, G.A.Methods Carboh...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H13/06C07B35/06
Inventor 杜宇国魏国华张磊蔡超程水红
Owner RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI
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